57543-66-5

Usage

Uses

Used in Pharmaceutical Industry:
2H-CHROMENE-3-CARBONITRILE is used as a precursor in the synthesis of various biologically active molecules and drugs. Its unique structure and properties contribute to the development of new compounds with potential therapeutic applications.
Used in Chemical Industry:
2H-CHROMENE-3-CARBONITRILE is used as a versatile intermediate for the production of other complex organic compounds. The cyano group in its structure allows for further chemical modifications and the creation of new compounds with diverse applications in various chemical processes.

InChI:InChI=1/C10H7NO/c11-6-8-5-9-3-1-2-4-10(9)12-7-8/h1-5H,7H2

Upstream product

• 62644-79-5 4-hydroxy-chroman-3-carbonitrile 
• 108-24-7 acetic anhydride 
• 90-02-8 salicylaldehyde 
• 107-13-1 acrylonitrile 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 51593-70-5 3-acetyl-2H-1-benzopyran 
• 51593-71-6 (2H-1-benzopyran-3-yl)phenylmethanone 
• 89197-60-4 3-cyano-chroman 
• 10185-46-3 chroman-3-ylmethanamine 
• 19090-04-1 chroman-3-one 
• 77479-42-6 C₁₈H₁₈N₂O₃S 
• 77479-41-5 C₂₃H₂₀N₂O₃S 
• 41873-72-7 chlorure d'acide chromene carboxylique-3 
• 76727-28-1 hydroxymethyl-3 chromanne 
• 115822-61-2 (2H-chromen-3-yl)methanol 
• 115822-64-5 chloromethyl-3 chromanne 
• 115822-58-7 chlorure d'acide chromanne carboxylique-3 

Relevant academic research and scientific papers

One pot, three component 1,3 dipolar cycloaddition: Regio and diastereoselective synthesis of spiropyrrolidinyl indenoquinoxaline derivatives

A competent and highly discriminating one-pot synthesis of highly diversified novel functionalized indenoquinoxalone grafted spiropyrrolidine linked chromene-3-carbonitrile conjugates accumulating three pharmocophoric cores, heterocyclic indenoquinoxalone, pyrrolidines and chromene-3-carbonitrile in a single molecular framework by means of 1,3-dipolar cycloaddition reaction between indenoquinoxalone, proline/benzyl amine and chromene-3-carbonitrile in ethanol under classical and microwave conditions is described. The three component 1,3-dipolar cycloaddition reaction proceeds via in situ generation of azomethine ylides by the decarboxylative condensation of indenoquinoxalone with proline/benzyl amine and their selectivity towards the endo cyclic double bonds of dipolarophile (chromene-3-carbonitrile) leading to the formation of highly functionalised regio- and diastereoselective molecular hybrids. This methodology exemplifies the green chemistry protocol such as mild reaction conditions, high yields, one-pot procedure and operational simplicity.

10-Camphorsulfonic acid ((±)-CSA) catalyzed facile one-pot synthesis of a new class of 2,5-disubstituted 1,3,4-oxadiazoles

A convenient and efficient one-pot synthesis of 2,5-disubstituted-1,3,4-oxadizoles is described. Various carboxylic acid hydrazides reacted efficiently with different carboxylic acid chlorides and 10-camphorsulfonic acid. This methodology was successfully

A spectroscopic insight into the interaction of chromene 1,2,4-oxadiazole-based compounds with bovine serum albumin

Four synthesized 2H-chromene-based 1,2,4-oxadiazole compounds (6a-6d) were studied for binding with bovine serum albumin (BSA) by different spectroscopic and thermodynamic analyses. A molecular docking program was used to find out the possible binding sites and binding affinity of 2H-chromene based 1,2,4-oxadiazole compounds with bovine serum albumin (BSA). The intrinsic fluorescence of BSA was quenched by these compounds through static quenching mechanism, and the estimated binding constant (Kb) value was found to be 1.5 × 103–10 × 103. The conformational changes of BSA were monitored by circular dichroism analysis, and it was observed that BSA is structurally stable in the presence of these compounds. The thermodynamic results indicated that the interaction process is spontaneous and the binding between oxadiazole compounds and BSA is mainly driven by hydrogen bonding and van der Waals forces. This study would be helpful to understand the biological benefits of oxadiazole-based compounds as well as the nature of interactions with biomolecules. Graphic abstract: [Figure not available: see fulltext.].

Synthesis and antimicrobial evaluation of novel urea derivatives from chromene based oxadiazole amines

A series of novel aryl ureides were synthesized based on oxadiazoles and different substituted aromatic amines. The intermediate amine, (3-(2H-chromen-3-yl)-1,2,4-oxadiazol-5-yl)methanamines (6a) was reacted with aromatic amines in presence of triphosgene

Synthesis, characterization, and antifungal activity of novel chromene oxadiazole based dithiocarbamates

A series of novel conjugated chromene oxadiazole-based dithiocarbamate (5a–i) derivatives have been synthesized from oxadiazole (4a–c) intermediates with carbon disulfide. The structures of all the newly synthesized compounds were established by IR, NMR, and Mass spectral analysis. The synthesized derivatives were screened for their antifungal activity against Aspergillus niger fungal strain and the results showed that some of the derivatives were found to exhibit good antifungal activity.

Synthesis of Pharmaceutically Relevant 2-Aminotetralin and 3-Aminochroman Derivatives via Enzymatic Reductive Amination

2-Aminotetralin and 3-aminochroman derivatives are key structural motifs present in a wide range of pharmaceutically important molecules. Herein, we report an effective biocatalytic approach towards these molecules through the enantioselective reductive coupling of 2-tetralones and 3-chromanones with a diverse range of primary amine partners. Metagenomic imine reductases (IREDs) were employed as the biocatalysts, obtaining high yields and enantiocomplementary selectivity for >15 examples at preparative scale, including the precursors to Ebalzotan, Robalzotan, Alnespirone and 5-OH-DPAT. We also present a convergent chemo-enzymatic total synthesis of the Parkinson's disease therapy Rotigotine in 63 % overall yield and 92 % ee.

Synthesis, cytotoxicity, and molecular docking of substituted 3-(2-methylbenzofuran-3-yl)-5-(phenoxymethyl)-1,2,4-oxadiazoles

A series of new benzofuran/oxadiazole hybrids (8a–n) was synthesized from 2H-chromene-3-carbonitriles (3a–c) through the multistep synthetic methodology, and these hybrids are known to exhibit anticancer activities. All the compounds were evaluated for their in vitro cytotoxicity against the HCT116 and MIA PaCa2 cell lines. Compounds 6a (IC50: 9.71 ± 1.9 μM), 6b (IC50: 7.48 ± 0.6 μM), and 6c (IC50: 3.27 ± 1.1 μM) displayed a significant cytotoxic activity, whereas compounds 8d and 8e exhibited good activity against both cell lines. The depletion of glycogen synthase kinase-3β (GSK3β) induces apoptosis through the inhibition of basal NF-κB activity in HCT116 colon cancer cells and MIA PaCa2 pancreatic cancer cells. Molecular docking of compounds 6a, 6b, 6c, 8d, and 8e with GSK3β demonstrated the best binding affinity, correlating with the biological activity assay. Furthermore, the structure–activity relationship of these novel compounds reveals promising features for their use in anticancer therapy.

Design and Synthesis of Novel 2-Substituted-Benzyl-5-(2-Methylbenzofuran-3-yl)-2H-Tetrazoles: Anti-Proliferative Activity

Abstract: A new series of 2,5-regioselective benzofuran-tetrazole hybrids (XIIIa–XIIIp) were synthesised from 2H-chromene-3-carbonitriles (IXa), (IXb) in multi steps approach under mild reaction conditions in good yields and evaluated their anti-proliferative activity against HCT116 and Miapaca2 cell lines. Wherein compounds (XIIIe) (IC50: 3.19 μM) and (XIIIm) (IC50: 2.25 μM) were displayed highest anti-proliferative activity in both cell lines. Molecular docking and SAR studies revealed the in vitro results with target Proto-oncogene tyrosine kinase Src protein.

Microwave-Assisted Rapid and Efficient Synthesis of New Series of Chromene-Based 1,2,4-Oxadiazole Derivatives and Evaluation of Antibacterial Activity with Molecular Docking Investigation

A new series of novel chromene-based oxadiazole derivatives were synthesized from a variety of chromene-based amidoximes with readily available carboxylic acids under conventional oil bath heating as well as under microwave irradiation. The use of commercially available EDCI and HOBt as coupling reagents in DMF combined with microwave heating resulted in high yields and purities of the product 1,2,4-oxadiazoles in an expeditious manner. This methodology is successfully applied to synthesize 18 numbers of new 2H-chromene-substituted 1,2,4-oxadiazole derivatives in good to high yields. The structure of the product was ascertained by X-ray crystallographic analysis. All the synthesized compounds were evaluated for their in vitro antibacterial activity against two different pathogenic bacterial strains, that is, Escherichia coli (MTCC614) and Klebsiella pneumoniae (MTCC4031). The obtained results from in vitro antimicrobial assays indicated that 6g and 6h exhibited good antibacterial activity nearer to the standard drug, gentamicin. The molecular docking studies showed that compounds 6g and 6h show hydrogen bonding interaction with the bacterial target DNA gyrase of E.?coli.

Discovery of (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide as potent and isoform selective ROCK2 inhibitors

ROCK1 and ROCK2 are highly homologous isoforms. Accumulated studies indicate that they have distinct different functions, and the development of isoform selective ROCK inhibitors will pave new roads for the treatment of various diseases. In this work, a series of amide-chroman derivatives were synthesized and biologically evaluated in order to develop potent and isoform selective ROCK2 inhibitors. Remarkably, (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide ((S)-7c) possessed ROCK2 inhibitory activity with an IC50 value of 3 nM and 22.7-fold isoform selectivity (vs. ROCK1). Molecular docking indicated that hydrophobic interactions were the key element for the high potency and isoform selectivity of (S)-7c. The binding free energies predicted by MM/GBSA were in good agreement with the experimental bioactivities, and the analysis of individual energy terms suggested that residue Lys105 in ROCK1 or Lys121 in ROCK2 was the key residue for the isoform selectivity of (S)-7c.